3-Chloroaniline

Description

m-Chloroaniline is used as an intermediate for pesticides, pharmaceuticals, and dyes. It is produced by lowpressure hydrogenation of 3-chloronitrobenzene in the liquid phase with noble metal and/or noble metal sulfide catalysts. The addition of metal oxides to the reaction helps avoid dehalogenation. The yield is approximately 98 %.

Chemical properties

3-Chloroaniline is a clear pale yellow to brown liquid, which becomes darker during storage, insoluble in water, but soluble in ethanol, ether and acid solution.

The Uses of 3-Chloroaniline

3-Chlorobenzenamine is used in the synthesis of pyrimidoazepine analogs as serotonin 5-HT2A and 5-HT2C receptor ligands for the treatment of obesity. Also used in the synthesis of novel COX-2 inhibito rs.

What are the applications of Application

3-Chloroaniline is the intermediate of the herbicide chloraniline, and the intermediate of the pharmaceutical diuretic antihypertensive drug hydrochlorothiazide, and can be used to produce azo dyes.
3-Chloroaniline was the only aniline compound to increase plasmaALT/GPT activity at 48 h. It is employed in the bioaugmentation of activated sludge.

Preparation

3-Chloroaniline is obtained by reducing 3-Nitrochlorobenzene with iron powder in the presence of ferrous sulfate.

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 7313, 1995 DOI: 10.1016/0040-4039(95)01474-V

General Description

Colorless to light amber liquid with a sweet odor.

Air & Water Reactions

Sensitive to prolonged exposure to air and light and tends to darken during storage. Insoluble in water.

Reactivity Profile

3-Chloroaniline is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents.

Fire Hazard

3-Chloroaniline is combustible.

Flammability and Explosibility

Non flammable

Safety Profile

Poison by ingestion, skin contact, subcutaneous, and intravenous routes. Mutation data reported. When heated to decomposition it emits toxic fumes of Cland NOx. See also ANILINE DYES.